TY - JOUR
T1 - Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis
AU - Shibata, Kouhei
AU - Takao, Ken Ichi
AU - Ogura, Akihiro
N1 - Funding Information:
This research was supported by JSPS KAKENHI Grant number 19K15571 and Keio Gijuku Academic Development Funds. We acknowledge Prof. Fumitoshi Kakiuchi, Prof. Takuya Kochi, and Shota Kanno at Keio University for GC measurements.
Publisher Copyright:
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PY - 2021/8/6
Y1 - 2021/8/6
N2 - A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindolines. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.
AB - A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindolines. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.
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U2 - 10.1021/acs.joc.1c00820
DO - 10.1021/acs.joc.1c00820
M3 - Article
AN - SCOPUS:85110961197
VL - 86
SP - 10067
EP - 10087
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 15
ER -